Dynamic kinetic resolution of bis-sulfinyl chlorides: A general enantiodivergent synthesis of C2-symmetric bis-sulfinate esters and bis-sulfoxides [4]

Journal of the American Chemical Society

Volumn 122, Issue 31, 2000, Pages 7598-7599

  Khiar, Noureddine ^a   Alcudia, Felipe ^b   Espartero, José Luis ^b   Rodríguez, Lourdes ^b   Fernández, Inmaculada ^b  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CHLORIDE; SULFOXIDE; SULFUR;

CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; LETTER; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0034625911     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000865c     Document Type: Letter

References (34)

1. For reviews on the synthesis and utilization in C-C bond formation of chiral sulfoxides see: (a) Solladié, G. Synthesis 1981, 185. (b) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (c) Kagan, H. B.; Diter, P. Organosulfur Chemistry; Page, P. C. B., Ed.; Academic Press: New York, 1998; Vol. 2, p 1. (d) Khiar, N.; Fernández, I.; Alcudia, A.; Alcudia, F. Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press Inc.; Stamford, 2000; Vol. 2, Chapter 3.
2. For reviews on the synthesis and utilization in C-C bond formation of chiral sulfoxides see: (a) Solladié, G. Synthesis 1981, 185. (b) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (c) Kagan, H. B.; Diter, P. Organosulfur Chemistry; Page, P. C. B., Ed.; Academic Press: New York, 1998; Vol. 2, p 1. (d) Khiar, N.; Fernández, I.; Alcudia, A.; Alcudia, F. Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press Inc.; Stamford, 2000; Vol. 2, Chapter 3.
3. For reviews on the synthesis and utilization in C-C bond formation of chiral sulfoxides see: (a) Solladié, G. Synthesis 1981, 185. (b) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (c) Kagan, H. B.; Diter, P. Organosulfur Chemistry; Page, P. C. B., Ed.; Academic Press: New York, 1998; Vol. 2, p 1. (d) Khiar, N.; Fernández, I.; Alcudia, A.; Alcudia, F. Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press Inc.; Stamford, 2000; Vol. 2, Chapter 3.
4. For reviews on the synthesis and utilization in C-C bond formation of chiral sulfoxides see: (a) Solladié, G. Synthesis 1981, 185. (b) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (c) Kagan, H. B.; Diter, P. Organosulfur Chemistry; Page, P. C. B., Ed.; Academic Press: New York, 1998; Vol. 2, p 1. (d) Khiar, N.; Fernández, I.; Alcudia, A.; Alcudia, F. Advances in Sulfur Chemistry; Rayner, C. M., Ed.; JAI Press Inc.; Stamford, 2000; Vol. 2, Chapter 3.
5. For previous use of chiral sulfoxides as ligands in transition metal catalysis see: (a) James, B. R.; McMillan, R. S. Can. J. Chem. 1977, 55, 3927. (b) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123. (c) Carreño, M. C.; García-Ruano, I. L.; Maestro, M. C.; Martín Cabrejas, L. M. Tetrahedron Asymmetry 1993, 4, 727. (d) Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 36, 8035.
6. For previous use of chiral sulfoxides as ligands in transition metal catalysis see: (a) James, B. R.; McMillan, R. S. Can. J. Chem. 1977, 55, 3927. (b) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123. (c) Carreño, M. C.; García-Ruano, I. L.; Maestro, M. C.; Martín Cabrejas, L. M. Tetrahedron Asymmetry 1993, 4, 727. (d) Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 36, 8035.
7. For previous use of chiral sulfoxides as ligands in transition metal catalysis see: (a) James, B. R.; McMillan, R. S. Can. J. Chem. 1977, 55, 3927. (b) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123. (c) Carreño, M. C.; García-Ruano, I. L.; Maestro, M. C.; Martín Cabrejas, L. M. Tetrahedron Asymmetry 1993, 4, 727. (d) Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 36, 8035.
8. For previous use of chiral sulfoxides as ligands in transition metal catalysis see: (a) James, B. R.; McMillan, R. S. Can. J. Chem. 1977, 55, 3927. (b) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123. (c) Carreño, M. C.; García-Ruano, I. L.; Maestro, M. C.; Martín Cabrejas, L. M. Tetrahedron Asymmetry 1993, 4, 727. (d) Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 36, 8035.
9. For previous use of sulfoxides in molecular recognition see: (a) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (b) Savage, P. B.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 10448 and references therein.
10. For previous use of sulfoxides in molecular recognition see: (a) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900. (b) Savage, P. B.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 10448 and references therein.
11. Yapp, D. T. T.; Rettig, S. J.; James, B. R.; Skov, K. A. Inorg. Chem. 1997, 36, 5635.
12. (a) Nieuwenhuyse, H.; Louw, R. J. Chem. Soc., Perkin Trans. 1 1973, 839.
13. (b) Mayarnoff, C. A.; Mayarnoff, B. E.; Tang, G.; Mislow, K. J. Am. Chem. Soc. 1973, 95, 5839.
14. (c) Skarzewski, J.; Ostrychartz, E.; Siedlecka, R. Tetrahedron: Asymmetry 1999, 10, 3457.
15. Douglass, I. B.; Farah, B. S.; Thomas, E. J. J. Org. Chem. 1961, 26, 1996.
16. 6 at 500 MHz: 4-(S,S), 5.76; 4-(R,R), 5.82: 4-(R,S), 5.79 and 5.84; 5-(S,S), 5.82; 5-(R,R), 5.87; 5-(R,S), 5.83 and 5.89.
17. For reviews on DKR see: (a) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (b) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 447. (d) Stecher, H.; Faber, K. Synthesis 1997, 1. (e) El Gihani, M. T.; Williams, J. M. Curr. Op. Chem. Biol. 1999, 3, 11.
18. For reviews on DKR see: (a) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (b) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 447. (d) Stecher, H.; Faber, K. Synthesis 1997, 1. (e) El Gihani, M. T.; Williams, J. M. Curr. Op. Chem. Biol. 1999, 3, 11.
19. For reviews on DKR see: (a) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (b) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 447. (d) Stecher, H.; Faber, K. Synthesis 1997, 1. (e) El Gihani, M. T.; Williams, J. M. Curr. Op. Chem. Biol. 1999, 3, 11.
20. For reviews on DKR see: (a) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (b) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 447. (d) Stecher, H.; Faber, K. Synthesis 1997, 1. (e) El Gihani, M. T.; Williams, J. M. Curr. Op. Chem. Biol. 1999, 3, 11.
21. For reviews on DKR see: (a) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475. (b) Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. (c) Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 447. (d) Stecher, H.; Faber, K. Synthesis 1997, 1. (e) El Gihani, M. T.; Williams, J. M. Curr. Op. Chem. Biol. 1999, 3, 11.
22. (a) Fernández, I.; Khiar, N.; Liera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6689.
23. (b) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1994, 35, 5719.
24. (c) El Ouazzani, H.; Khiar, N.; Fernández, I.; Alcudia, F. J. Org. Chem. 1997, 62, 287.
25. (d) Khiar, N.; Fernández, I.; Roca, A.; Benabra, A.; Alcudia, F. Tetrahedron Lett. 1999, 40, 5779.
26. 1HNMR spectra of the crude mixture of signals at 5.8-6.7 ppm corresponding to the vinyl sulfoxides.
27. (a) Andersen, K. K.; Gaffield, W.; Papanikolau, N. E.; Foley, J. W.; Perkins, R. I. J. Am. Chem. Soc. 1964, 86, 5637.
28. (b) Jacobus, J.; Mislow, K. J. Am. Chem. Soc. 1967, 89, 5228.
29. 2-symmetric bis-sulfoxide enantiomer is always present in negligible amount (0 to 1%, Table 1).
30. For a mathematical treatment of the kinetics in DKR, see: (a) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (b) Kitamura, M.: Tokunaga, M.; Noyori, R. Tetrahedron 1993, 49, 1853.
31. For a mathematical treatment of the kinetics in DKR, see: (a) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (b) Kitamura, M.: Tokunaga, M.; Noyori, R. Tetrahedron 1993, 49, 1853.
32. (a) Berry, R. S. J. Chem. Phys. 1960, 32, 933.
33. (b) Mikolajczyk, M.; Drabowicz, J.: Bujnicki, B. Tetrahedron Lett. 1985, 26, 5699.
34. (c) Okuyama, T. In The Chemistry of Sulphinic Acids, Esters and Their derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, England, 1990; Chapter 21.